New York Halloween Getaways Upstate

Find out if the Legend of Sleepy Hollow and the tale of the Headless Horseman are true for a New York Halloween.Tarrytown becomes Horseman's Hollow during the fall fright season.

Within a few hours of well-lit Manhattan, the dark dreary forests, fog-shrouded bogs and haunted houses of the Hudson Valley come to life for a spooky New York Halloween. This tranquil region along the Hudson River and upstate New York in Westchester, Dutchess, Orange and Ulster Counties is bursting with fun things themed to the holiday.

First, you should know that if you’re up for a road trip, the entire state of New York has a Haunted History Trail featuring 65 of the sickest attractions in every county, on a 400-mile tour across the state. It’s open year round but gets extra traffic during October. So, whether you just enjoy the fun, festive occasion for its pumpkins, candy and costumes, or if you prefer a more fearful celebration, New York’s Hudson Valley has a weekend getaway option for everyone.

Finding New York Halloween Fun

Like everything else, when demanding New Yorkers want a haunted house, they want a good haunted house. Forget about Manhattan, where scary things happen all the time. If your kids and teens want a candy-collecting weekend away, with a fun, scary haunted house, a real haunted house, or a haunted house tour, an upstate New York Halloween can supply it.

From Tarrytown to Woodstock to New Paltz, there are lots of other autumn attractions for a New York Halloween including hayrides, museums, nature hikes, leaf peeking, corn mazes, pick your own apple and pumpkin farms, and much, much more.

Once you’ve spooked yourself to tears, you can calm down at one of the many hotels in the Tarrytown area; several fall getaway packages include breakfast and Wi-Fi with a double room, as well as local shuttles for the car-less. The Westchester County Tourism Office has a listing of what’s available.

Low Freak Out Factor: Hudson Valley’s Great Jack O’Lantern Blaze

The great Blaze at the Van Cortland Manor is Hudson Valley’s biggest Halloween event. Visitors get to experience the sight of over 7,000 hand-carved jack o’ lanterns and wander through the historic property which is all decked-out for Halloween. In past years, the pumpkins have been astonishing: dinosaurs roam the earth and pirates set sail for buried treasure, mummies and pyramids came straight out of Ancient Egypt, and giant spiders create monstrous webs. Snakes, shrunken heads, and ghosts entertained visitors and there was even an undersea aquarium. Visit Jack O’ Lantern Blaze or call 914/631-8200 to purchase tickets and, remember, if they are sold out, there’s still a possibility that local hotels featured on their website have tickets if you book a room with them.

Sleepy Hollow Becomes Horseman’s Hollow

In the Tarrytown area of Westchester, Philipsburg Manor transforms into a haunted landscape in celebration of the annual Hudson Valley Horseman’s Hollow. This year, there are 12 nights of fun rated for ages 10+ that come with an explicit warning (isn’t this neat?) that says: “This event is NOT suitable for small children and it is not suitable for adults who are claustrophobic, have heart or respiratory conditions, are prone to seizures, or have other chronic health conditions.” Enter at your own risk!

Anyone tough enough to take it can wander through the candle-lit surroundings and spooky grounds associated with this demonic fable, while avoiding confrontation with witches, goblins and uncanny apparitions in a legendary literary village. The Hollow boasts state-of-the-art special effects and professional actors, so you’re sure to enjoy your fright.

And the Real Sleepy Hollow Is?

Loving the Fox TX series of the same name? “Sleepy Hollow” fans can tour Westchester County’s actual village and drop in (or drop out) at the famous, 85-acre Sleepy Hollow Cemetery. It’s known for burying the very rich and very famous, including beauty magnate Elizabeth Arden; NY Public Library benefactors Brooke Astor and Andrew Carnegie; car scion Walter Chrysler and his later nemesis, labor leader and AF of L founder Samuel Gompers; author of “Legend of Sleepy Hollow” Washington Irving; and the local baron William Rockefeller.

There are day and evening guided tours, but the popular New York Halloween storytelling tour done several times in October is not advisable for kids. Get tickets and information at Sleepy Hollow Cemetery.

Orange County Has High Freak Out Hauntings

What about Pure Terror Screampark? Honestly, images of The Necropolis and The Coven, among their 6 haunted houses, made us jump when their website loaded. Located at 299 Museum Village Road, Monroe, NY 10950 in who-knows-where Orange County, it is just 5 miles from the Woodbury Commons shopping outlet, where you can really freak out spending money. This Catskills scare-atorium has six separately themed fright zones, including our favorite “Butchers Revenge.”

Their website says you cannot carry babies through the exhibits, nor are exhibits recommended for pregnant women.

New York’s Headless Horseman Attraction

When it comes to New York Halloween scares, however, farther north in Ulster is the place to be — whether you want to scream all night or just enjoy some Halloween activities. The Headless Horseman, a collection of hayrides and haunted houses at 778 Broadway, Route 9W in Ulster Park, NY 12487, has been named the #1 Haunted Hayride in the country by AOL Travel and we can see why.

Not only does it have a one-mile-long themed hayride, but it also offers a spooky corn maze and several haunted houses — 10 attractions in total. There are ghoulish performers and plenty of shops for candied apples, scary gifts, and yummy pumpkin pie. Older kids can go on the hayride and tour the haunted houses, while the little ones enjoy sweet treats and entertaining shows. In fact, two Saturday mornings in October are dedicated to “A Tiny Taste of Terror.” If you’re really into terror, book the separate “Great Room Escape,” a 60-minute escape experience you can wriggle out of with others. The Headless Horseman is open Friday through Sunday from mid-September to early November; also on select Thursdays.

Not only are the leaves gorgeous during autumn in upstate New York, but there are also plenty of other family-friendly activities. Kelder’s Farm has a 100-acre Pick-Your-Own field with pumpkins and a corn maze that everyone can get lost in. The farm is open daily for pumpkin, sweet corn and squash picking (apples are mostly gone by Halloween); mini-golf, a jumping pillow, and other seasonal fun. Be sure to pick up their farm-raised free-range chicken or grass-fed cuts of beef to take home.

Ulster County hosts animal sanctuaries where you can visit the animals and learn how to protect them from cruelty. Both the Woodstock Farm Animal Sanctuary and the Catskill Animal Sanctuary offer an educational experience on how to help our furry friends and our environment. Children will have fun petting the animals and teenagers will learn to save them from abuse; call ahead for tour times as visiting hours are usually limited to weekends. And check out Hallowoodstock, the last weekend before Halloween.

Ulster is also home to the world’s largest kaleidoscope and you can have a seat in this huge silo and enjoy a show on the ceiling above you. There’s no better weekend base than the Emerson Resort & Spa, a rural New York Halloween getaway that hosts this famous kaleidoscope and lots of fun family activities and adventures. If you want to play in the outdoors, this may be a better choice for your family than staying in Tarrytown.

Greene County’s Northern Catskills is Horrifying

The Great Northern Catskills should not be forgotten, especially for a weekend getaway, since many hotels are offering autumn and Halloween packages. Among the fun attractions we’ve caught over the years, you can join ages 8+ at the Zombie Hunter Wars at Hunter Mountain; enroll your shaggy mop in the Tannersville Scarecrow Contest or stomp yourselves silly at the Children’s Halloween Monster Mash Party, in Catskill at the Brookside Campground.

Some of the Catskills lodging properties have themed packages; your go-to, forever-gone resource for New York Halloween terror in the northern Catskills is the tourism office of Great Northern Catskills of Greene County.

This story was accurate when it was published. Please be sure to confirm all rates and details directly with the companies in question, and stay up to date with current events to ensure a safe and successful trip.